It’s been a few years since I’ve bought a physical CD, and ripping music is already super-easy thanks to iTunes and iTunes Match. Books, however, are much harder to “rip”. (There is actual ripping involved.)
I still frequently buy physical books from Amazon, and often re-buy them in Kindle or iBooks format to read on my phone and iPad. This always feels like a backwards, bullshit requirement.
An AutoRip for books would be totally great, but is an unlikely prospect in the near future for the reasons Frommer outlines. Until book piracy skyrockets or publishers stop praying for the halcyon days of dead tree-only books, there’s not going to be a digital copy version of your past purchased novels.